1-Hydroxybenzotriazole → HCID 178466808, compound

HRID 1096902Notes

Reaction equation

HRID 1096902 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[CH2:23]([O:25][C:26]1[CH:27]=[C:28]([CH:32]=[C:33]([O:42][CH2:43][CH3:44])[C:34]=1[C:35]1[CH:40]=[CH:39][N:38]=[C:37]([F:41])[CH:36]=1)[C:29]([OH:31])=O)[CH3:24].Cl.[NH:46]1[C:50]([C:51]2[CH:52]=[C:53]3[C:63](=[CH:64][CH:65]=2)[O:62][C:56]2([CH2:61][CH2:60][NH:59][CH2:58][CH2:57]2)[CH2:55][C:54]3=[O:66])=[N:49][N:48]=[N:47]1>O.CN(C=O)C.CCN(CC)CC>[CH2:43]([O:42][C:33]1[CH:32]=[C:28]([C:29]([N:59]2[CH2:60][CH2:61][C:56]3([CH2:55][C:54](=[O:66])[C:53]4[C:63](=[CH:64][CH:65]=[C:51]([C:50]5[NH:49][N:48]=[N:47][N:46]=5)[CH:52]=4)[O:62]3)[CH2:57][CH2:58]2)=[O:31])[CH:27]=[C:26]([O:25][CH2:23][CH3:24])[C:34]=1[C:35]1[CH:40]=[CH:39][N:38]=[C:37]([F:41])[CH:36]=1)[CH3:44]

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667820673,5-Diethoxy-4-(2-fluoropyridin-4-yl)benzoic acidHCID 178479612HCID 178479612, compound

Product 1

HCID 178466808HCID 178466808, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Et3N (290 μL), HOBT (160 mg) and WSC hydrochloride (200 mg) were added to a DMF (8 mL) solution of 3,5-diethoxy-4-(2-fluoropyridin-4-yl)benzoic acid (266 mg) and 6-(tetrazol-5-yl)spiro[chroman-2,4′-piperidin]-4-one hydrochloride (325 mg), and stirred overnight at room temperature. Water was added to the reaction liquid, the formed solid was taken out through filtration, and the solid was washed with water and ether. The solid was dried under reduced pressure to obtain the title compound. 1H-NMR (400 MHz, DMSO-d6) δ: 8.42 (1H, d, J=4.0 Hz), 8.25-8.20 (2H, m), 7.32 (1H, d, J=8.0 Hz), 7.29-7.26 (1H, m), 7.10 (1H, s), 6.76 (2H, s), 4.32-4.18 (1H, m), 4.08 (4H, q, J=8.0 Hz), 3.64-3.20 (3H, m), 2.98 (2H, s), 2.10-1.75 (4H, m), 1.17 (6H, t, J=8.0 Hz). MS [M+H]+=573.

Workup

  1. filtrationthe formed solid was taken out through filtration
  2. washthe solid was washed with water and ether
  3. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-cbd83d281eec4bf4aefdbd57e234afab
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

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